Family-friendly holiday rentals in The Annex, Old Toronto

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Top-rated family-friendly rentals in The Annex, Old Toronto

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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Guest favourite
A cozy living area features a grey sofa and two matching armchairs, all positioned on a neutral area rug. A modern arc floor lamp provides soft lighting, while framed art adorns the walls. A small glass side table sits beside the sofa, enhancing the space's functionality.
Flat in Annex
4.93 out of 5 average rating, 216 reviews

Cute Private Apartment near University of Toronto

This cozy main floor apartment with private walk out patio, located on a quiet street in the beautiful Annex neighbourhood. Free parking Laundry in building Shared backyard 5 minute walk to subway (Christie Station) 5 minute walk to Bloor Street, the restaurants and bars of Korea Town, and historic Christie Pits Park. Walking distance to University of Toronto and George Brown College Casa Loma campus. There are a lot of great restaurants, bars and local grocery stores within a short walk.

Guest favourite
A spacious sleeping area features a brand new bed with a quilted beige coverlet, complemented by two bedside lamps. Exposed brick walls add character, while colorful artwork hangs above the bed. A cozy sofa is visible to the side, enhancing the inviting atmosphere.
Guest suite in Little Italy
4.88 out of 5 average rating, 140 reviews

Loft-Style Private Studio Little Italy/Ossington

From the exposed brick, to original artwork, to massive private bathroom with double vanity, this basement suite in our home has been renovated and decorated to feel like a loft. The double bed is brand new with a 16" mattress sure to deliver an excellent night's sleep. You will find a brand new, 42" smart TV resting on a unique mantlepiece refashioned from an antique upright piano, as well as a kitchenette with convection oven/air fryer, Keurig coffeemaker, and stainless steel mini fridge.

Guest favourite
A warm and inviting living area features exposed brick walls and a large wooden dining table surrounded by black chairs. Soft lighting from a vintage chandelier casts a gentle glow over a cozy sofa and a stylish entertainment unit, creating a sense of comfort.
Flat in Annex
4.94 out of 5 average rating, 118 reviews

Luxurious Annex/Yorkville 1300 Sq Ft & Parking

Beautifully appointed, top quality furnishings & amenities , spacious Yorkville/Annex rental. Full 1300 sq foot. apartment located within a Heritage Victorian Brownstone! Exceptionally located, walking distance to subway, restaurants and all the sights! Walk to Casa Loma, Royal Ontario Museum & Yorkville. Parking, Wifi, Chromcast, Fibe TV, Local High Def TV included. Fully equipped gourmet kitchen. Air Conditioned. Digital safe for valuables. Treat yourself to pantry snacks, coffee & tea.

Guest favourite
A modern living space is presented, featuring a sleek kitchen area with wooden cabinetry and stainless steel appliances. A soft gray sofa with decorative pillows faces the windows, allowing natural light to illuminate the room. A glass partition adds a touch of elegance.
Apartment in Yorkville
4.93 out of 5 average rating, 115 reviews

*Gorgeous & professional condo in Yorkville*

Owned by a traveller and importer who spends a lot of his time in the Mediterranean, this residence poises your downtown Toronto stay smack-dab in the heart of one of North America’s most prodigious communities, Yorkville, while simultaneously experiencing comfortable and cultivated condominium ambiance. This residence is perfect for travellers for short-term stays and business professionals working remotely for longer-term stays who need a comfortable and intelligent living environment.

Guest favourite
A cozy sleeping area is presented with a spacious bed, featuring soft bedding and decorative pillows. Nightstands flank the bed, providing small plants and ambient lighting. A calming nature print is displayed above the bed, enhancing the serene environment.
Home in Annex
4.87 out of 5 average rating, 100 reviews

Annex Haven: 1 Bedroom plus Den

This centrally located private space is newly updated with new flooring, furniture, and bathroom. It includes a separate entrance with its own kitchen and laundry. Very quiet residential neighbourhood with old growth trees. Walking distance to Christie subway station or Dupont subway station. Be downtown within 20 minutes. Close to Koreatown and many great restaurants on Bloor Street. 5 min walk to 4 grocery stores and LCBO. Basement space not suitable for people over 6 feet tall.

Guest favourite
A living area features a comfortable brown sofa with red cushions and a rustic coffee table at its center. A flat-screen television sits on a white stand, while potted plants add greenery to the space. Natural light enters through sliding glass doors.
Home in Little Portugal
4.91 out of 5 average rating, 210 reviews

Charming coach house / guest house downtown

Private and secluded, completely separated, fully serviced and renovated guest house / urban cottage with a beautiful private patio nestled among the mature trees of Dufferin Grove - one of Toronto's most vibrant and interesting neighbourhoods. Find quiet, peace and tranquility in a private oasis, tucked away behind trees and the residential streets, located in the middle of Toronto's trendiest urban centres: Little Italy, Dundas West, Ossington, Little Portugal and Queen West.

Top guest favourite
A cozy living area features a grey sofa adorned with colorful cushions, complemented by a glass coffee table sitting on a softly patterned rug. Two wooden chairs provide additional seating. Natural light filters through a nearby window, highlighting the hardwood floors.
Home in University
4.82 out of 5 average rating, 183 reviews

Two story home & garden in vibrant neighbourhood

Newly renovated heritage home in the heart of one of Toronto's most vibrant neighborhoods. Perfect for families, the home features hardwood floors, lots of natural light, and very comfy beds. Conveniently located steps from the subway on a residential street, you are close to many great restaurants & blocks from the U of T and Kensington market. Not far from Scotiabank arena & Rogers centre - for concerts and sporting events. Patio and garden are yours to enjoy. Pets welcome.

Guest favourite
A stylish living space features an eye-catching geometric wallpaper, complemented by a contemporary wooden sideboard and a gray sectional sofa. A small round table and a two-person bar table are positioned near large windows that offer expansive city views.
Apartment in Yorkville
4.93 out of 5 average rating, 189 reviews

Beautiful 1 Bedroom Yorkville Condo (IG-hotspot)

Pamper yourself with everything Yorkville has to offer with this professionally decorated, NYC inspired condo at the heart of Toronto's most exclusive address with complimentary valet parking. Queen size bed, sofa bed in living room, 2 person bar table, work station and a 55" Smart TV to accommodate all your needs. Contemporary art by local artist throughout with high end furniture and Miele appliances. South facing lake/city views through expansive floor to ceiling windows.

Guest favourite
A glass table is positioned near large windows, offering an unobstructed view of the city skyline. Two modern chairs are placed around the table, with a small potted plant and a decorative item enhancing the scene. The background features tall buildings and hints of greenery.
Apartment in Yorkville
4.88 out of 5 average rating, 162 reviews

Steps to Four Seasons Hotel Yorkville Condo

Unobstructed panoramic view in the heart of upscale Yorkville. Minute walk to Bay subway station, Whole Foods, ROM and U of T and high-end restaurants. Easy parking @ 74 Yorkville for $20 (daytime). Around the corner from Toronto's main luxury shopping hub, Yonge + Bloor. *Upscale neighborhood *Highspeed WIFI *Walk score of 96 *Transit score of 93 *Bike score of 98 (rentable Bixi bikes nearby) *Fully equipped kitchen *Full-sized washer/dryer *Gym in building

Superhost
A living area is presented with two blue armchairs positioned beside a low coffee table. A flat-screen TV is mounted on the wall above a gas fireplace. Light filters in through a large window, illuminating built-in shelves filled with decorative items.
Townhouse in Yorkville
4.81 out of 5 average rating, 101 reviews

Stunning Yorkville Townhome Backing onto Park

Situated in the heart of Yorkville, this 3 bedroom 2.5 bathroom townhouse with views overlooking Ramsden Park, is the ideal oasis for families, couples, or people travelling for work. The space features a bright sun-filled interior featuring a gas fireplace, WIFI, Smart TV with all apps and fully equipped kitchen. The home backs onto green space with a wonderful back deck and eating area.

Guest favourite
A bright living area features a comfortable grey sofa paired with a patterned armchair. A large mirror reflects the light, enhancing the open feel. Decorative art pieces and indoor plants add a touch of warmth, while large windows allow natural light to fill the space.
Home in Wychwood
4.81 out of 5 average rating, 181 reviews

Contemporary cozy home in the Annex

This 2 bed/2bath home is located in the more northern part of the downtown core called West Annex/Seaton Village and is on a cul de sac. Steps from TTC, Yorkville, art galleries, restos & more. The small urban-chic, clean and bright home boasts two balconies off either bed & a spacious backyard off kitchen. Permit No: STR-2010-GZSXPH Application Reference No: 3383-645

Guest favourite
The living room features a spacious leather sectional sofa facing a central coffee table. Natural light fills the area through multiple large windows. A brick fireplace adds warmth, while a staircase with glass railing leads to the upper levels. Potted plants bring a touch of greenery.
Home in Annex
4.88 out of 5 average rating, 260 reviews

Bright, Stunning Victorian Townhouse in the Annex

Newly renovated, 3 level, 2-bedroom sun-filled unit, situated in the Annex. Brick fireplace, central air conditioning and heating, wooden floors and exposed brick. Steps away from Bloor St, coffee shops, restaurants, shops, galleries, parks and much much more. Short walk to Bathurst and Spadina Subway, Casa Loma, Yorkville, University of Toronto, and museums.

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Quick stats about holiday rentals that are family-friendly in The Annex, Old Toronto

  • Total holiday rentals

    Explore 70 holiday rentals in The Annex, Old Toronto

  • Nightly prices starting at

    The Annex, Old Toronto holiday rentals start at £15 per night before taxes and fees

  • Verified guest reviews

    Over 1,820 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    70 of The Annex, Old Toronto holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across The Annex, Old Toronto rentals

  • 4.7 Average rating

    The Annex, Old Toronto stays receive an average rating of 4.7 out of 5 from guests

  • Nearby attractions

    The Annex, Old Toronto’s top spots include Royal Ontario Museum, Bata Shoe Museum and Spadina Station

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